This would be a lot cuter if Hugh Hefner was the grandfather of the Shannon Twins. Instead, he's their lover.
Rating: 3.2 / 5.0
Hugh Hefner and Crystal Harris are married! Send in your best wishes to the couple now.
Rating: 3.2 / 5.0
The Playboy boss pats his top girlfriend on the (pregnant?) belly. This rumor proved to be false, as Holly Madison was never knocked up.
Rating: 3.1 / 5.0
In regular clothes, that is. Dude normally wears pajamas, or probably less when he gets naked with his many girlfriends. But here, he almost looks like a regular old guy! Almost.
Rating: 3.0 / 5.0
Aubrey O'Day and Hugh Hefner look thrilled to be hanging out at this Playboy party, don't they? It's okay to smile, guys.
Rating: 3.0 / 5.0
Is it all over for Crystal Harris and Hugh Hefner? Sources say the former walked out on the latter five days prior to their wedding date.
Rating: 3.0 / 5.0
Hugh Hefner is seen here with Crystal Harris and Anna Sophia Berglund. Sources say he moved on from the former with the latter.
Rating: 3.0 / 5.0
Hugh Hefner tries to keep up with one of the Shannon twins in this picture from a party thrown in honor of Aubrey O'Day. Can you imagine these two having sex? Yikes.
Rating: 2.9 / 5.0
Holly Madison and Hugh Hefner are having a lot of sex as they try to have a baby. Sorry. We're just reporting the facts, as relayed to us by Holly herself. Hard to blame Hugh, she's kind of a looker.
Rating: 2.9 / 5.0
Sherlyn Chopra gives Hugh Hefner a squeeze in this photo. The former will become the first Indian to get naked in Playboy.
Rating: 2.9 / 5.0
Hugh Hefner looks almost alive in this picture. It's courtesy of the Iron Man 2 premiere in Los Angeles.
Rating: 2.6 / 5.0
Pssst, Hef. Thanks for putting me in your magazine. I'll repay you later... if you know what I mean!
Rating: 2.5 / 5.0

Hugh Hefner Biography

Holly and Hugh
Hugh Henfer is the envy of millions of men around the world. Despite not being close to a spring chicken, the Playboy founder has a... More »
Chicago, Illinois
Full Name
Hugh Marston Hefner